Did Yudhishthira lie more than once?


No, Yudhishtira did not lie in this case.
And this fact is without any hidden or deep meaning.

When we relate "truth" or Satya with just "information", then we can often find contradictions in the behaviours of righteous people. Dharma doesn't solely rely on correct/incorrect information. If that was the case, then all computers will become DhArmik!

PAndava-s were specifically ordered or agreed to remain disguised for the last 1 year after being defeated in dice game. This is found in SabhA parva:

Sakuni then said,--'The old king hath given ye back all your wealth. That is well. But, O bull of the Bharata race, listen to me, there is a stake of great value. Either defeated by ye at dice, dressed in deer skins we shall enter the great forest and live there for twelve years passing the whole of the thirteenth year in some inhabited region, unrecognised, and if recognised return to an exile of another twelve years; or vanquished by us, dressed in deer skins ye shall, with Krishna (Draupadi), live for twelve years in the woods passing the whole of the thirteenth year unrecognised, in some inhabited region. If recognised, an exile of another twelve years is to be the consequence. On the expiry of the thirteenth year, each is to have his kingdom surrendered by the other. O Yudhishthira, with this resolution, play with us, O Bharata, casting the dice.

Yudhishtira was a just king and his duty was towards the well being of the people of his kingdom. Hence for him, the Dharma was to get his kingdom back after 13 years. The condition of remaining unrecognised, was set & agreed as a stipulation. So he Had to disguise himself as someone else. Hence this was neither a lie in technical way nor it was Adharma.

BTW on side note,

"Did Yudhishthira lied more than once?"

Probably you meant "other" as the "supposed" lie which Yudhishtira spoke for Ashwatthama to defeat Drona. According to Krishna, even that was also acceptable in that context. I have discussed that in this answer:

Behold, however, truth as practised is exceedingly difficult to be understood as regards its essential attributes.
Truth may be unutterable, and even falsehood may be utterable where falsehood would become truth and truth would become falsehood. ...
On an occasion of marriage, or of enjoying a woman, or when life is in danger, or when one's entire property is about to be taken away, or for the sake of a BrAhmana, falsehood may be uttered.

So technically even though it was not a perfect truth, it was still DhArmik.

IMO, probably Yudhishtira might have never moved on completely from that game changing half-truth which ultimately resulted in his preceptor's death. He always might have felt attached with it even though Krishna adviced that event to be righteous. That could be the reason, why he had to finally go through a small test in the heaven-hell.

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